Trimethyl orthoformate → N-[4-(1-hydroxyiminoethyl)phenyl]-N'-allyloxycarbonylmethylurea

HRID 1111053Notes

Reaction equation

HRID 1111053 reaction equation
[CH2:1]([O:4][C:5](=[O:8])[CH2:6][NH2:7])[CH:2]=[CH2:3].[CH3:9][C:10]([C:12]1[CH:17]=[CH:16][C:15]([N:18]=[C:19]=[O:20])=[CH:14][CH:13]=1)=O.Cl.[NH2:22][OH:23].C(OC)(OC)OC>C1COCC1.N1C=CC=CC=1>[OH:23][N:22]=[C:10]([C:12]1[CH:17]=[CH:16][C:15]([NH:18][C:19]([NH:7][CH2:6][C:5]([O:4][CH2:1][CH:2]=[CH2:3])=[O:8])=[O:20])=[CH:14][CH:13]=1)[CH3:9]

Participants

7

Reactant 4

HCID 9005Trimethyl orthoformateHCID 994524-Acetylphenyl isocyanateHCID 108831Allyl glycinateHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 131716732N-[4-(1-hydroxyiminoethyl)phenyl]-N'-allyloxycarbonylmethylurea

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 0.02 mol glycine allyl ester in 40 mL of THF is added dropwise to a solution of 0.02 mol of 4-isocyanatoacetophenone and 5 mL of pyridine in 40 mL of THF and the reaction mixture is stirred for 3 hours. The solvent is then removed by rotary evaporator. The residue is dispersed in 50 mL of CH3OH, and 0.022 mol of hydroxylamine hydrochloride and 0.06 mol of trimethyl orthoformate are added. The reaction mixture is heated to reflux for 1 hour. The solvent is removed by rotary evaporator to give the product, N-[4-(1-hydroxyiminoethyl)phenyl]-N'-allyloxycarbonylmethylurea.

Workup

  1. customThe solvent is then removed by rotary evaporator
  2. additionThe residue is dispersed in 50 mL of CH3OH
  3. temperatureThe reaction mixture is heated
  4. temperatureto reflux for 1 hour
  5. customThe solvent is removed by rotary evaporator

Sources & evidence

ORD record
ord-2b73cd12e7f6451c8e70c0932770b2ce
Source dataset
uspto-grants-1990_12
Patent number
US04977272

Reaction notes

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